#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:15:55 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179621 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/85/4508519.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4508519
loop_
_publ_author_name
'Bala, Sukhen'
'Goswami, Arijit'
'Sengupta, Satirtha'
'Ganguly, Sumi'
'Bhattacharya, Sudeshna'
'Khanra, Sumit'
'Mondal, Raju'
_publ_section_title
;
 Metal-Directed Formation of Molecular Helix, Cage, and Grid Using an
 Asymmetric Pyridine-Pyrazole Based Bis-Chelating Ligand and Properties
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5068
_journal_paper_doi               10.1021/cg401236b
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C17 H15 N7 O'
_chemical_formula_weight         333.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.777(9)
_cell_angle_beta                 95.364(9)
_cell_angle_gamma                92.319(9)
_cell_formula_units_Z            2
_cell_length_a                   5.3664(12)
_cell_length_b                   10.819(3)
_cell_length_c                   14.774(3)
_cell_measurement_reflns_used    1642
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.51
_cell_volume                     796.0(3)
_computing_cell_refinement       'Bruker APEX-2'
_computing_data_collection       'Bruker APEX-2'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-2 CCD area detector'
_diffrn_measurement_method       '/w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_sigmaI/netI    0.0928
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10229
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.48
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Estimated minimum and maximum transmission:  0.4203  0.7457 
SADABS v.2.03 (Bruker, 2001), R(int)=0.0537 before correction
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Niddle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0759
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1755
_refine_ls_wR_factor_ref         0.1974
_reflns_number_gt                1915
_reflns_number_total             3346
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg401236b_si_004.cif
_cod_data_source_block           13sb023_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4508519
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O -0.2270(4) 1.1761(2) 0.13357(15) 0.0424(6) Uani 1 1 d .
N1 N 0.0091(4) 1.3963(2) -0.21777(18) 0.0382(6) Uani 1 1 d .
C1 C -0.0490(6) 1.4696(3) -0.2713(2) 0.0431(8) Uani 1 1 d .
H1 H 0.054(7) 1.464(4) -0.323(3) 0.071(12) Uiso 1 1 d .
C1S C -0.0083(8) 0.3142(4) 0.4349(3) 0.0630(11) Uani 1 1 d .
N1S N 0.1788(8) 0.3447(4) 0.4843(3) 0.0935(13) Uani 1 1 d .
N2 N 0.1402(4) 1.2473(2) -0.10411(19) 0.0331(6) Uani 1 1 d .
H222 H 0.213(8) 1.226(4) -0.154(3) 0.074(14) Uiso 1 1 d .
C2 C -0.2491(6) 1.5481(3) -0.2586(2) 0.0401(8) Uani 1 1 d .
H2 H -0.276(5) 1.602(3) -0.296(2) 0.035(8) Uiso 1 1 d .
C2S C -0.2428(8) 0.2763(6) 0.3732(3) 0.0805(14) Uani 1 1 d .
H2SC H -0.2118 0.2489 0.3063 0.072(12) Uiso 1 1 calc R
H2SB H -0.3443 0.3505 0.3881 0.20(4) Uiso 1 1 calc R
H2SA H -0.3291 0.2043 0.3841 0.13(2) Uiso 1 1 calc R
N3 N 0.1780(4) 1.1841(2) -0.04148(17) 0.0323(6) Uani 1 1 d .
C3 C -0.4001(6) 1.5484(3) -0.1884(2) 0.0385(7) Uani 1 1 d .
H3 H -0.533(6) 1.604(3) -0.175(2) 0.041(8) Uiso 1 1 d .
N4 N 0.1719(5) 1.1120(2) 0.11837(18) 0.0328(6) Uani 1 1 d .
H444 H 0.301(7) 1.098(3) 0.085(3) 0.058(11) Uiso 1 1 d .
C4 C -0.3474(5) 1.4717(3) -0.1334(2) 0.0369(7) Uani 1 1 d .
H4 H -0.437(7) 1.473(4) -0.079(3) 0.069(11) Uiso 1 1 d .
N5 N 0.1738(4) 1.0619(2) 0.19086(16) 0.0338(6) Uani 1 1 d .
C5 C -0.1378(5) 1.3970(3) -0.14900(19) 0.0304(6) Uani 1 1 d .
N6 N 0.5646(4) 0.8558(2) 0.27056(17) 0.0366(6) Uani 1 1 d .
C6 C -0.0686(5) 1.3179(3) -0.0909(2) 0.0303(6) Uani 1 1 d .
C7 C -0.1695(5) 1.2983(3) -0.0142(2) 0.0324(7) Uani 1 1 d .
H7 H -0.308(6) 1.335(3) 0.013(2) 0.039(8) Uiso 1 1 d .
C8 C -0.0107(5) 1.2156(3) 0.0135(2) 0.0302(6) Uani 1 1 d .
C9 C -0.0336(5) 1.1673(3) 0.0932(2) 0.0321(7) Uani 1 1 d .
C10 C 0.3610(5) 0.9963(3) 0.2003(2) 0.0338(7) Uani 1 1 d .
H10 H 0.483(5) 0.981(3) 0.1588(19) 0.028(7) Uiso 1 1 d .
C11 C 0.3773(5) 0.9366(3) 0.2744(2) 0.0319(7) Uani 1 1 d .
C12 C 0.2097(6) 0.9588(3) 0.3438(2) 0.0444(8) Uani 1 1 d .
H12 H 0.085(8) 1.006(4) 0.337(3) 0.080(13) Uiso 1 1 d .
C13 C 0.2328(6) 0.8984(4) 0.4108(2) 0.0488(9) Uani 1 1 d .
H13 H 0.137(7) 0.918(4) 0.469(3) 0.075(12) Uiso 1 1 d .
C14 C 0.4256(6) 0.8176(3) 0.4082(2) 0.0433(8) Uani 1 1 d .
H14 H 0.442(5) 0.769(3) 0.460(2) 0.042(8) Uiso 1 1 d .
C15 C 0.5841(6) 0.7988(3) 0.3370(2) 0.0379(7) Uani 1 1 d .
H15 H 0.715(6) 0.737(3) 0.3330(19) 0.037(8) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C5 118.0(3)
N1 C1 C2 123.6(3)
N1 C1 H1 117(2)
C2 C1 H1 120(2)
N1S C1S C2S 179.8(7)
N3 N2 C6 113.0(2)
N3 N2 H222 120(3)
C6 N2 H222 124(3)
C3 C2 C1 118.3(3)
C3 C2 H2 121.5(18)
C1 C2 H2 120.1(18)
C1S C2S H2SC 109.5
C1S C2S H2SB 109.5
H2SC C2S H2SB 109.5
C1S C2S H2SA 109.5
H2SC C2S H2SA 109.5
H2SB C2S H2SA 109.5
C8 N3 N2 104.3(2)
C4 C3 C2 119.3(3)
C4 C3 H3 119.7(19)
C2 C3 H3 120.9(19)
C9 N4 N5 120.8(2)
C9 N4 H444 122(2)
N5 N4 H444 116(2)
C3 C4 C5 119.1(3)
C3 C4 H4 124(2)
C5 C4 H4 117(2)
C10 N5 N4 116.0(2)
N1 C5 C4 121.7(3)
N1 C5 C6 116.9(2)
C4 C5 C6 121.4(3)
C15 N6 C11 117.0(2)
N2 C6 C7 105.6(2)
N2 C6 C5 121.8(2)
C7 C6 C5 132.6(3)
C6 C7 C8 105.1(3)
C6 C7 H7 126.1(19)
C8 C7 H7 128.8(19)
N3 C8 C7 112.0(2)
N3 C8 C9 121.3(2)
C7 C8 C9 126.7(3)
O1 C9 N4 123.3(3)
O1 C9 C8 121.8(2)
N4 C9 C8 114.9(2)
N5 C10 C11 120.1(3)
N5 C10 H10 121.7(17)
C11 C10 H10 118.1(17)
N6 C11 C12 121.9(3)
N6 C11 C10 115.4(2)
C12 C11 C10 122.6(3)
C13 C12 C11 119.8(3)
C13 C12 H12 125(3)
C11 C12 H12 115(3)
C12 C13 C14 118.5(3)
C12 C13 H13 126(2)
C14 C13 H13 115(2)
C13 C14 C15 118.8(3)
C13 C14 H14 118.4(16)
C15 C14 H14 122.8(16)
N6 C15 C14 123.9(3)
N6 C15 H15 117.6(17)
C14 C15 H15 118.5(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.234(3)
N1 C1 1.331(4)
N1 C5 1.341(3)
C1 C2 1.381(4)
C1 H1 0.97(4)
C1S N1S 1.146(5)
C1S C2S 1.435(6)
N2 N3 1.338(3)
N2 C6 1.371(4)
N2 H222 0.83(4)
C2 C3 1.375(4)
C2 H2 0.94(3)
C2S H2SC 0.9600
C2S H2SB 0.9600
C2S H2SA 0.9600
N3 C8 1.337(4)
C3 C4 1.373(4)
C3 H3 0.94(3)
N4 C9 1.359(3)
N4 N5 1.361(3)
N4 H444 0.87(4)
C4 C5 1.400(4)
C4 H4 0.97(4)
N5 C10 1.278(3)
C5 C6 1.447(4)
N6 C15 1.330(4)
N6 C11 1.350(3)
C6 C7 1.379(4)
C7 C8 1.396(4)
C7 H7 0.91(3)
C8 C9 1.461(4)
C10 C11 1.454(4)
C10 H10 0.92(3)
C11 C12 1.390(4)
C12 C13 1.366(5)
C12 H12 0.88(4)
C13 C14 1.376(4)
C13 H13 1.01(4)
C14 C15 1.379(4)
C14 H14 1.07(3)
C15 H15 0.98(3)
